Pancratistatin

Base Information

• Chemical Name: Pancratistatin
• CAS No.: 96203-70-2
• Molecular Formula: C14H15NO8
• Molecular Weight: 325.2708
• NSC Number: 349156
• UNII: 4GUM4B7K5B
• DSSTox Substance ID: DTXSID501315881
• Nikkaji Number: J362.301G
• Wikipedia: Pancratistatin
• Wikidata: Q7130395
• NCI Thesaurus Code: C1184
• ChEMBL ID: CHEMBL419335
• Mol file: 96203-70-2.mol

Synonyms:pancratistatin

Chemical Property of Pancratistatin

Chemical Property:

• Appearance/Colour: Colorless crystal or crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 260 °C (decomp)
• Boiling Point: 661.4°Cat760mmHg
• PKA: 7.72±0.70(Predicted)
• Flash Point: 353.8°C
• PSA: 148.71000
• Density: 1.824g/cm³
• LogP: -1.89750
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 325.07976644
• Heavy Atom Count: 23
• Complexity: 503

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Pancratistatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1OC2=C(O1)C(=C3C(=C2)C4C(C(C(C(C4O)O)O)O)NC3=O)O
• Isomeric SMILES: C1OC2=C(O1)C(=C3C(=C2)[C@@H]4[C@H]([C@@H]([C@@H]([C@H]([C@@H]4O)O)O)O)NC3=O)O
• Uses: Pancratistatin acts as an anti-cancer compound that initiates cell-death in cancer cells.

Technology Process of Pancratistatin

There total 185 articles about Pancratistatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(1R,2S,3S,4S,4aR,11bR)-7-Benzyloxy-1,2,3,4-tetrahydroxy-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one → pancratistatin (96203-70-2,96281-31-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethyl acetate;

DOI:10.1021/ja00117a046

Reference yield: 91.0%

(+)-pancratistatin tetraacetate (166115-49-7) → pancratistatin (96203-70-2,96281-31-1)

Guidance literature:

With sodium methylate; In methanol; at 25 ℃;

DOI:10.1021/jacs.8b12123

Reference yield: 90.0%

<(+/-)-(1β,2α,3β,4β,4aβ,11bα)>-1,3,4,4a,5,11b-Hexahydro-1,3,4-trihydroxy-2,7-bis(phenylmethoxy)<1,3>dioxolo<4,5-j>phenanthridin-6-(2H)-one (120882-33-9) → (+)-pancratistatin (96203-70-2,120962-18-7,96281-31-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethyl acetate; for 0.5h;

DOI:10.1021/ja00195a039

upstream raw materials:

<(+/-)-(1β,2α,3β,4β,4aβ,11bα)>-1,3,4,4a,5,11b-Hexahydro-1,3,4-trihydroxy-2,7-bis(phenylmethoxy)<1,3>dioxolo<4,5-j>phenanthridin-6-(2H)-one

1,2-Dihydroxyphenyl diethylcarbamate

Downstream raw materials:

4,7-dihydroxy-[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one

Refernces

• 1、 Hernandez, Lucas W.,Pospech, Jola,Kl?ckner, Ulrich,Bingham, Tanner W.,Sarlah, David. "Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene". . p. 15656 - 15659. Retrieved 2017.
• 2、 Bingham, Tanner W.,Hernandez, Lucas W.,Olson, Daniel G.,Svec, Riley L.,Hergenrother, Paul J.,Sarlah, David. "Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene". supporting information. p. 657 - 670. Retrieved 2019/01/08.
• 3、 Potter, Tyler J.,Ellman, Jonathan A.. "Total Synthesis of (+)-Pancratistatin by the Rh(III)-Catalyzed Addition of a Densely Functionalized Benzamide to a Sugar-Derived Nitroalkene". supporting information. p. 2985 - 2988. Retrieved 2017/06/07.